As far as the leverage goes, tfrasca is right. The longer the arm (distance hinge to pressure point) the more advantage there is. Moving the peg all the way down to where the stand meets the ground will give you that.
Here in Holland we have pretty strict license requirements, but that means we get a lot of training. One of the main tricks my instructor taught me, has helped me hugely in putting any big bike on its stand. I'm 5'10" and weigh 155 pounds, so it's not always an easy task.
The trick is to no want to pull the back backwards onto its stand, but grab the handlebar and a rail/seat/support at the end, push the bike stand on the ground and straighten out your body. This will help you push down on the stand and lift the bike over the stand at the same time.
I might be kicking in the biggest open door in motorcycle history, but I've noticed a lot of differences in riding technique in countries (also did my test in Australia, very very different).